Sean Penn TV Appearances You Didn’t Know About, Ranked

Before there was ‘The First’ on Hulu, there was ‘Little House on the Prairie,’ ‘Two and a Half Men’ and ‘Friends’

Since embarking upon his career as a feature film actor — in Taps, nearly 37 years ago — Sean Penn has had about as distinguished run as anyone in his generation: critical acclaim; dozens of award nominations; and two Best Actor Oscar wins (for Mystic River and Milk), a record he shares with only seven other performers. (Daniel Day-Lewis has bested them all with three.)

This week, though, Penn takes on a new challenge: headlining an episodic TV series. In The First, a Hulu original created by Beau Willimon, Penn plays Tom Hagerty, an astronaut preparing to be one of the first humans to land on Mars. Perhaps what motivated Penn to take on the challenge was good reports of Willimon from his ex-wife Robin Wright, whom Willimon cast in Netflix’s House Of Cards (another of Willimon’s creations). Perhaps Penn wanted to get one letter closer to his EGOT.

Or perhaps he just wanted to get back to his roots — TV, where Penn started his career. Much of his earliest juvenilia isn’t easily accessible, but Penn has periodically broken up his film work by returning to TV with appearances over the years. (This, of course, doesn’t include his guest spots on the myriad late-night shows; it does, however, include when he’s played himself on fictional talk shows like Larry Sanders or sitcoms like Two and a Half Men.) Let’s count them down!

9) ‘Ellen,’ Season 5, Episode 8,“Emma”

Arriving early in the first post-coming out season of the mid-1990s sitcom Ellen (also its final season), “Emma” finds the titular Ellen (Ellen DeGeneres) chancing upon Oscar winner Emma Thompson (as herself) making out with a woman. Ellen gets herself hired as Thompson’s temporary assistant and encourages her to come out. Thompson’s prepared to go public with her sexuality, but not with the other big secret she’s been keeping: She’s not actually British; she was born in Dayton, Ohio. However, before Thompson can make her announcement at an awards banquet, she gets upstaged by a taped message from her current co-star, Penn, in which he states that he is gay.

The episode now stands as a tragically ironic document in terms of how wrong the character Ellen is about the minimal damage Thompson will do to her career by coming out — by the end, Emma’s been outed by a tabloid and is working as a restaurant server, presaging the many hard years DeGeneres faced after she came out — but Penn is the worst thing about it. He couldn’t even be bothered to film with his co-stars, and while pretending to be gay for a sitcom storyline was probably a bold show of allyship in 1997, he’s unconvincing in the role of Sean Penn. I suspect he sent the show his first and only take.

8) ‘Little House On The Prairie,’ Season 1, Episode 11, “The Voice Of Tinker Jones” and Season 1, Episode 21, “Money Crop”

Penn’s father Leo, who passed away in 1998, was a prolific TV director who found opportunities to cast his middle son, Sean, in non-speaking roles during his early teen years. “Wait, you’re saying Sean Penn was better as an adolescent extra than he was as himself on Ellen?” I sure am.

7) ‘The Larry Sanders Show,’ Season 6, Episode 11, “Flip”

Penn joins Jerry Seinfeld, Jim Carrey, Tom Petty and Carol Burnett, among many others, for the star-studded series finale of The Larry Sanders Show, playing himself as a guest on the final episode of the fake talk show. Penn apparently isn’t a gifted improviser, and his anecdote about a pushy “stewardess” trying to make him stow his screenplay on his flight down from the Bay Area goes nowhere when Larry (Garry Shandling) asks what the script in question was about and he can’t even come up with an answer.

Penn is there to promote his next film: an adaptation of David Rabe’s play Hurlyburly, co-starring his then-wife Robin Wright, Kevin Spacey and… Garry Shandling. At a commercial break, Penn confides to Larry that Shandling was a nightmare to work with — desperately insecure, surrounded by acting coaches and hitting on Wright between takes. Though Penn’s performance here is nearly as lackluster as on Ellen, it’s memorable for being the only time we ever get confirmation that Garry Shandling exists in the Larry Sanders universe.

6) ‘Family Guy,’ Season 15, Episode 6, “Hot Shots”

Primarily revolving around Lois and Peter falling victim to online conspiracy theories and deciding not to vaccinate their baby, Stewie, “Hot Shots” is — like every other Family Guy episode I’ve ever seen — also ground to a dead-stop by cutaway non sequitur “jokes.” In this case, those include a transphobic joke about the Wachowskis; an ableist joke about a crossing guard having jurisdiction over law enforcement officers who use wheelchairs; and jokes about CSI: Miami, E.T. and The Dark Knight that aren’t offensive but are weirdly old for an episode that aired in 2016.

Penn’s last pre-Taps role is in this TV movie, based on a true story; Penn plays Don, best friend to murder victim Randy. This is another project that seems in retrospect to have been created as the answer in a future showbiz trivia quiz: co-starring with Penn is Gary McCleery, soon to join Penn in Taps; and both Jennifer Jason Leigh and Anthony Edwards, both of whom would later rejoin Penn in Fast Times at Ridgemont High.

3) ‘Two And A Half Men,’ Season 2, Episode 1, “Back Off Mary Poppins”

Charlie (Charlie Sheen) orders Alan (Jon Cryer) to clear out for the night so that Charlie can host some friends for scotch and cigars and an intimate discussion about their lives. Charlie is irritated that Alan thinks it’s a support group, and Alan is irritated that he hasn’t been invited because Charlie doesn’t consider them friends. Alan’s even more hurt when he discovers that members of Charlie’s not-a-support-group include Elvis Costello (as himself), Harry Dean Stanton (as himself) and Penn (as… you get it).

Penn puts some thought and craft into this performance: He’s convincingly sheepish asking if he’s the only one who gets up in the middle of the night to pee; bitterly calls out Costello’s practice of borrowing his stories to turn them into songs; and proves he can take a joke when Alan dorkily asks, “Why don’t you do funny stuff like you used to?” Of all Penn’s TV performances as “himself,” it’s the most vulnerable and the most charming.

2) ‘Friends,’ Season 8, Episodes 6 and 7, “The One With The Halloween Party” and “The One With The Stain”

The only post-fame/pre-The First TV role where Penn’s not playing himself! Phoebe (Lisa Kudrow) meets Eric (Penn) at a Halloween party where he’s strangely forward with her for a total stranger. Soon they figure out that he’s mistaken her for her twin sister Ursula (Kudrow again), to whom Eric is engaged. That Phoebe is also drawn to Eric — a sweet second-grade teacher — is complicated not just by his betrothal to her sister but because everything Ursula has told Eric about herself is a lie: She wasn’t in the Peace Corps; she hasn’t been “saving herself” for him; and she doesn’t teach at a “top-secret elementary school for the children of spies.”

By the end of “Halloween Party,” Phoebe has told Eric the truth about Ursula, and he starts in “Stain” by telling Phoebe that he and Ursula broke up and asking Phoebe out. Unfortunately, Phoebe’s face reminds him of Ursula’s, and of how angry he still is about their fraudulent relationship. Things only get more tangled when Ursula comes by in Phoebe’s absence and impersonates her to get Eric to have sex with her.

Eric and Phoebe aren’t meant to be, but it’s refreshing to see Penn not just play an actual character on TV, but give him enough dimension and endearing awkwardness to make the viewer forget who’s playing him.

1) ‘The First’

It’s pretty clear Hulu is hoping for a Handmaid’s Tale-sized hit with this series, which brings together an Oscar-nominated writer (Willimon, for the 2011 George Clooney film Ides of March); an Oscar-nominated director (Agnieszka Holland, for the 2011 foreign language film In Darkness); and a multiple-Oscar-winning star (Penn). If this were premiering 15 years ago, there’s no question its ambitious premise and high production values would make it an unmissable hit. But in 2018, it’s… fine?

Okay, it’s so self-consciously IMPORTANT that it verges on a parody of Prestige TV. The first episode finds Penn’s character doing a few things I don’t necessarily believe Penn himself has ever done — clean up a party; make a sandwich for a child; be kind to a woman over 40. But he does have nice chemistry with Anna Jacoby-Heron as his troubled daughter; I buy both that their relationship has been difficult and that he’s sincerely eager to mend it. So despite the show’s generally off-putting Emmy-begging, Penn’s performance manages to earn the top spot because, unlike in so many of the others on this list, he’s actually trying.